24,25-Dihydroxycholecalciferol

24,25-Dihydroxycholecalciferol, also known as 24,25-dihydroxyvitamin D₃ and (24R)-hydroxycalcidiol (abbreviated as 24(R),25-(OH)₂D₃),^[1] is a compound which is closely related to 1,25-dihydroxyvitamin D₃, the active form of vitamin D₃. Like vitamin D₃ itself and calcifediol (25-hydroxyvitamin D₃), it is inactive as a hormone both in vitro^[2] and in vivo.^[3] It was first identified in 1972 in the laboratory of Hector DeLuca and Michael F. Holick.^[4]

24,25-Dihydroxycholecalciferol

Names
IUPAC name (6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol
Other names 24,25-dihydroxyvitamin D3 (24R)-hydroxycalcifediol (24R)-hydroxycalcidiol
Identifiers
CAS Number	40013-87-4 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL47183 Y
ChemSpider	4939193 Y
ECHA InfoCard	100.049.754
PubChem CID	6434253
UNII	0AXX2V8L5Z Y
CompTox Dashboard (EPA)	DTXSID501028177
InChI InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22+,23-,24+,25?,27-/m1/s1 Y Key: FCKJYANJHNLEEP-SRLFHJKTSA-N Y InChI=1/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22+,23-,24+,25?,27-/m1/s1 Key: FCKJYANJHNLEEP-SRLFHJKTBM
SMILES O[C@@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CCC(O)C(O)(C)C)C
Properties
Chemical formula	C27H44O3
Molar mass	416.63 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Formation and significance

24,25-dihydroxyvitamin D₃ is formed from 25-hydroxyvitamin D₃ by the action of CYP24A1 (25-hydroxyvitamin D3-24-hydroxylase). CYP24A1 appears to be "a multicatalytic enzyme catalyzing most, if not all, of the reactions in the C-24/C-23 pathway of 25-OH-D₃ metabolism."^[5]

It has been proposed that 24,25-dihydroxyvitamin D₃ is a metabolite of 25-hydroxyvitamin D₃ which is destined for excretion.^[5]

It is not known whether the compound might also have some physiologically significant activity. Some evidence of a possible receptor has been obtained.^[6]

Because 24,25-dihydroxycholecalciferol is considered an inactive metabolite and its significance is that its concentration is expected to decrease in case of mutations inactivating the vitamin D 24-hydroxylase gene.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

[[File:

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

|alt=Vitamin D Synthesis Pathway (view / edit)]]

Vitamin D Synthesis Pathway (view / edit)

1. The interactive pathway map can be edited at WikiPathways: "VitaminDSynthesis_WP1531".